


Old Friend, Annoying Friend

by The_Whip_Hand_81



Category: Bill Hader - Fandom, IT, It:Chapter 2
Genre: 69, Alternate Universe - No Pennywise (IT), Angst, Bill Hader - Freeform, Bill Hader's fucking hot, Crazy for You by Madonna, Crushes, Cunnilingus, Derry, F/M, Face-Sitting, Fluffy Smut, Hotel Sex, IT - Freeform, IT: Chapter 2 - Freeform, Making Love, Not a horror story, Richie Tozier & Reader - Freeform, Richie Tozier - Freeform, Richie and Reader, The Losers Club, Unrequited Love, Vaginal Fingering, Wedding, angsty, immature Richie, slow dance, tender love
Language: English
Status: Completed
Published: 2019-12-04
Updated: 2019-12-04
Packaged: 2021-02-26 02:07:26
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 8,242
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21675739
Author URL: https://archiveofourown.org/users/The_Whip_Hand_81/pseuds/The_Whip_Hand_81
Summary: You come back to Derry after 27 years for your best friend's wedding, dreading the reunion of old friends, especially one in particular, Richie Tozier. Prim and proper you dont have time for Trash Mouth's nonsense but not for long. He might just win you over with his charms and updated look.
Relationships: Bill Hader & Reader, Bill Hader & You, Bill Hader/Original Female Character(s), Richie Tozier/Reader, Richie Tozier/You
Comments: 4
Kudos: 98





	1. Chapter 1

**Author's Note:**

> I do not own any of these characters. I borrowed them. Nothing like the book/film just used the cast of characters as buffers so...  
> I haven't written anything in exactly ONE year to this day I'm publishing this first part of the story which is pretty cool. Not intentional at all! So, needless to say, it's been a year since I've used my imagination and put it down for strangers to read. I hope it's okay and readable. Just an idea that I liked.

You are returning to your childhood hometown of Derry for the first time in 27 years. Your best friend since diapers, Beverly, is getting married and wanted to have the ceremony in town where you both grew up. You cringe at the thought of playing catch up with old friends and family members you neglected to keep in contact with for all those years ago when you moved as far away from small town life as possible and into the Big Apple. 

You climb out of the cab that just dropped you off at the town’s only hotel, “The Derry Town House”. A three storied brick building that looked more like a haunted hotel lost in time from the 1920s. You grab your luggage and exhale as you stare up at the lit up facade. 

The cab driver hollers out the passenger window, almost in jest, “Have a goodnight. Oh and welcome to Derry.” 

“Thanks…” you softly reply as fix the hem of your pleated skirt and ascend the steps into the hotel. 

You push open the mahogany doors into the dimly lit lobby where concierge was already serving a single patron. You slowly and quietly glance around the beautifully furnished room, pretending to busy yourself with the antiquated lamps while you wait your turn to be served when a shrill man’s voice began complaining to the staff behind the counter. 

“Are you fuckin’ kidding me right now? I reserved that suite 4 months ago!” the nasally voiced man yelled. 

You try not to look over the magazine shelf to watch but couldn’t help yourself so you just peer over the top. 

“We’re sorry, Mr. Tozier, but there seems to have been some kind of mix up…” the nervous teenager said as she typed on the hotel computer. 

You stop at the name, “Tozier…?” 

The man continues to holler, “A mix up? There shouldn’t BE a mix up if I paid for this room four months in advance! Don’t you know who I am?” 

The two staff members look at each other and slowly shake their heads. 

“Seriously?! I am the only person to make it out of this one horse town! Richie Tozier...the stand up comedian?...” he looks at their expressionless faces, his eyes in disbelief, “you know?....’the fun’s just beginning?’” 

The staff workers are still not fazed. 

Your brain suddenly floods your head with prepubescent memories by just hearing his full name and don’t know whether to hide behind the lounge chair or get another room the next town over. You haven’t seen Richie since you were both teenagers and, although he was in your circle of friends, you weren't very close with him. Growing up, Richie was constantly the center of attention and everyone loved his sarcastic and sometimes harsh sense of humor. Everyone except you. Not that you didn’t have a sense of humor, there was just something about him that you could not understand. For some reason, everything he did, everything he said rubbed you the wrong way. Especially since that time you spent together at summer camp...that time you never told anyone about. Not even Beverly. You found Richie extremely annoying so you kept everyone else around as a buffer or you just kept to yourself. Who knows? Maybe he grew out of it? 

Richie pushes his black rimmed glasses up, “Listen-,” he squints down at the teenage girl’s name tag on her blouse, “-JAN. I just flew in from LA, I had two fucking layovers because of the crappy weather in the midwest, my cab broke down on the way to this shit town and all I want to do is go to my suite, take a nice hot shower, get shitfaced and pass out on the bed until this hokey ass wedding event is over...what can I do to rectify this situation?” 

Jan scrolls through the reservations once more and answers, “I’m sorry, Mr Tozier, but this suite was also reserved by a Ms [Your first name/last name] for the same dates...I don’t know how that happened…”

Richie straightens up with furrowed brows, “Wait...I know that name..”

You walk up to the counter beside Richie and hand the staff member your ID with a smile, ignoring him to your right. “Hello, my name is [Y/N], I’d like to check in, please.” 

Richie looks down at you with disbelief and gives you a once over, his voice low and tame, “[Y/N]?”

Jan happily hands you the room key when you finally look up at him with a forced smile, “Hello, Richard. You look...,” you scan his outfit of a black zip jacket and dingy jeans and his messy wavy hair with five o clock shadow, “....alive and well.” 

Richie stares at your fit frame in awe, “Wow, you look amazing...what the fuck happened to me?” 

“Time, I suppose,” you begin to walk away with your rolling luggage in hand as Richie chases after you. 

“Hey, wait up! I need your help.” 

Your foot on the first step up, you stop, “With what?” 

Richie slowly inhales and presses his lips together, “There was a mix up with the room. They double-booked it and I reserved the room 4 months ago and I really need to sleep…” 

You tilt your head, “But the room is mine. I’m not going to give it to you just because there was a glitch in the system.” 

“[Y/N], please, I’m begging you. I don’t have any other place to go. That’s a big suite, there’s a pull out couch I can sleep on. You can have the stupid bed. Just- please, don’t leave me in the lurch, man...it’s only for a couple days until this shit show is over. I’ll pay you!” 

You can see the desperation and exhaustion behind those thick glasses and exhale heavily, “Fine.” 

“YES! THANK YOU! I CAN KISS YOU!...can I kiss you?” 

“NO!” you yell as you walk up the stairs. 

“Right, right. I’ll get my things…” Richie runs back to the desk and grabs his luggage and yells over to the staff behind the counter, “You see that? I won! I still get the room so fuck you, Jan -- well, not YOU, the computer. Fuck the computer…but you, too,” he scurries up the stairs behind you. 

You open the door to the suite and turn on the light. It is a large living space with a sofa and a king size bed toward the back against the wall and a full bathroom. You stand at the doorway admiring the beauty of the room when Richie brushes passed you and enters. He runs over to the bed and flopped back onto it.  
“Ooooooh, this feels niiiice…” He props up on his elbows to look over at you, “You wanna climb on top of me, see how nice it feels?”

You roll your eyes and close the door behind you, “Is this how you’re going to act the entire time we’re locked in this room together?”

Richie sits up, legs dangling off the side of the bed, “Oh, right, I forgot. You’re the one without a sense of humor.” He springs up to walk over to the couch. 

You roll your luggage to the closet, “I do too have a sense of humor! You’re not funny is all.” You begin to hang up your dresses. 

Stunned silence for a moment then a chuckle, “I’m not funny? Tell that to the millions of people who come see my shows and download my podcasts, lady. I’m fuckin’ hilarious.” 

“Well, Jan and the other staff never heard of you so…” 

Richie walks up to you organizing your clothes, “That’s because they’re uncultured swine living in Derry! Nobody knows anything outside this town! And -- are you putting your clothes in color order?”

Not looking at him, you answer, “I sure am. Is that a problem with you?” 

“Yeah, you’re fucking weird.” 

You stop to look at him, “You went on the Late Show and danced with orangutans and I’m the weird one?!” 

He smiles from ear to ear, “Ah, you saw that one, eh? Yeah, that was pretty great. You watch follow me?”

“Nope. I only saw it because Beverly sent me the link on Facebook. She keeps up with your life, not me.” 

Richie sits on the coffee table behind you, watching you bend over, picking up more clothes to be hung, “Beverly. She’s quite a gal. She’s the only reason why I came. If it had been any of you other losers, I’d never go through the trouble.” 

You frowned, “I wouldn’t have invited you to my wedding anyway. Why so close to Beverly? I’ve never seen you guys hang out together….unless you guys hooked up?” you turn to look at him inquizzatively. 

“Like the way you and I did back in summer camp, 1990?” he cocked his brow. 

You spun around in embarrassment, “You remember that?!” 

Richie licked his bottom lip and smiled like the cheshire cat, “Oh, [Y/N], how can a teenage boy ever forget --” 

You press your hands against your ears, air tight, cutting him off “LALALALALA! Please stop talking! I’m going to take a shower now!” You quickly fumble for your toiletry bag and run for the bathroom. You lock the door behind you and look at your reflection in the mirror. 

“Only six more days of him...only six more days…” you whisper to yourself. 

*

You exit the shower with a towel wrapped around your head, another wrapped around your wet body and a green face mask on when the bathroom door bursts open. Through the plume of steam you see a bright flash and hear a cackling laughter. 

You scream in shock, “DID YOU JUST TAKE A PICTURE OF ME IN MY TOWEL?!” 

You see another flash through the clearing steam and Richie about to run out of the bathroom, “You really should lock the door when you’re in the bathroom…” 

“RICHIE, YOU SON OF A BITCH!” you scream as you chase him into the living room, holding tightly the towel wrapped around your body. “DELETE THOSE PICTURES!” 

Richie holds his arm with his phone above his head as you desperately try to jump up and grab it from him. He cackles some more, “You’re so teeny! You’ll never reach this high--” just as he finished his sentence, you punch him in the stomach knocking the phone and the wind out of him. He collapses to the floor in a fit of coughs as you try to search his phone for the photos but his phone is locked. You shove the phone under his nose, angrily, “Type in the password and delete those pictures!” 

He coughs one last time and slowly gets up on his knees, “Okay, okay…” he unlocks the phone and deletes the photos, “See? Deleted.” He stands up and smooths out his shirt, “You know the situation could’ve been a lot worse...I could’ve caught you sitting on the toilet.” 

“Oh, shut up!” 

*

Once you remove your facial mask and got into your two piece black silk pajamas, you exit the bathroom to see Richie leaning against the couch, waiting for his turn for the shower. His arms crossed across his chest and a frown on his face, “It’s about damn time.” He looks at your pajamas with eyebrows raised, “If there was ever an outfit that turned a ‘hard-on’ into a ‘hard off’, those pajamas would be it.” 

You step up to his chest and look up at him, you squint your eyes with annoyance, “And what would you have me wear to bed, Richie? A sheer nightie with a G-string and fishnet stockings?” 

He jokes, “Well, not the fishnet stockings.” 

You grunt as you walk to your bed, not turning back, “Goodnight, Richard.”

“Goodnight, darling!” he sarcastically calls out to you. 

Richie enters the bathroom and locks the door. He turns on the shower and looks at his exhausted reflection in the damp mirror, the scent of your shower gel and body lotion still lingers in the air. He takes off his glasses and places them on the sink countertop when he notices the pile of clothes you were wearing earlier that you left on the floor. 

He frowns as he thinks to himself, ‘Mrs Perfect forgot to pick up her dirty laundry off the floor…’ He nudged the pile with his sneaker and saw your bra come out of the pile. He arched his brow and he picks it up and looks at the tag for the size, “...[your bra size]...she always had big tits…” he flings it back onto the pile of dirty clothes when he notices something red and lacy on the pile. Richie squats down and picks up your red lace bikini panties. He purses his lips as he thinks and stands up in front of the mirror. With the scent of you still lingering in the air and the steam mellowing his nerves, Richie brings your panties to his nose and inhaled deeply. His body shivers as he inhales longer a second time and his jeans suddenly become tight. He glances at the door to see if he locked it and pulls off his jeans and boxers. He already has precum leaking from his tip when he began pumping his shaft, up and down. Slowly at first, then faster and faster as his other hand kept your panties to his nose as he imagined he was fucking you from behind at this very moment, in front of this very bathroom mirror. He was gonna lose it soon and didn’t want to make any noise so he stuffed your panties into his mouth, moans muffled, as he accidentally ejaculated onto your pile of clothes. He just stared down at it in shock for a moment then thought, ‘Well, it’s already dirty...she won’t notice.’ 

***  
The sun’s rays pour through the blinds of the hotel room onto your face. You begin to stir and turn over onto your stomach to bury your face in the pillow. You let out a long sigh falling back to sleep when a loud sound of glass crashing to the floor makes you shoot up to sitting position. With wild and blurry eyes, you see Richie standing in his plaid boxers and Led Zeppelin t-shirt a few feet from your bed holding an empty tray that once held a bowl of fruit and a cup of coffee that are now shattered on the floor. He is frozen in embarrassment then yells, “SURPRISE! I got you breakfast in bed!” 

You slam your body back down on the bed and cover your head with the duvet and grumble, “Call the front desk to clean that up, please....” 

“Sure!” Richie begins to walk away to call but then comes back, “I would but I kinda sorta told the kid at the front desk to go fuck herself last night…”

You sit back up, yelling, “Are you for real, Richie?!” 

“To be fair, I told the computer to go fuck itself soooo not really the kid…well, I told her to fuck off a little.” 

“God dammit, Richie!” you fling the quilt off your body and put your feet on the floor, “why can’t you shut your mouth for once in your OUCH! FUCK!” You lift your foot off the floor and see a big sliver of porcelain under your heel, blood dripping onto the floor. 

Richie’s eyes widen, “Oh my God, you’re bleeding. Wait there, don’t move.” Richie rushes toward you, side stepping the glass and mess. Without warning, he swoops you up into his arms carrying you bridal style into the bathroom. You hadn’t been in a man’s grasp in 3 years and it felt pretty nice...even if it was Richie. 

He places you onto the bathroom countertop and rummages through the cabinet near your head. He pulls out a few bandages and alcohol wipes. Richie quickly pulls out the piece of glass and takes a small towel to your foot, pressing it firmly. 

“OW! Jesus, Tozier, you’re hurting me…” you whine as you look at his intense face, concentrating and serious for once. 

“Hold still, you big baby, I have to stop the bleeding, get it to clot before cleaning it...you have adorable feet, by the way…” He pulls the towel away, looks at the gash and begins to clean it. 

You tilt your head to the side with a small smile, “Where did you learn this stuff? Do you have kids?” 

His eyes never leaving your foot, he stifles a laugh, “No. Stanley taught me when he was in Boys Scouts. I had lots of practice patching up my little cousins growing up.” 

Still smiling down at him, Richie glances up and gives a small smile back, “What’s the smile for? A moment ago you were dying of blood loss.” 

Your cheeks turn pink as he stands up in front of you, “I don’t know. Picturing you patching up kids with scraped knees is sweet. A side I didn’t think you had.” 

Richie steps closer, “If you think that’s sweet, then I should tell you how many puppies I saved from a fire just last night,” he steps closer, “Or last week when I helped an old lady cross the street. I bet you’re creaming in your panties right now just thinking of those good deeds, aren’t you?” 

“UUGGHH!” you shove him back and hop off the counter, “You were almost genuine for a minute there.” 

“Yeah, it’s hard to be normal for that long.” 

“I’m getting dressed for brunch. Stay in the bathroom.” You close the door, leaving him in the bathroom. 

“What?! Come on, man, what am I supposed to do in here this whole time?!” he looks at the dirty pile of clothes you left on the floor from last night and smiles, “Never mind. I’m good.” 

*  
You and Richie step out into the sunny summer morning walking toward your cars in the parking lot. You are dressed in a peach colored sundress and white wedge shoes, your hair done up in a cute messy bun. Your sunkissed makeup made you look like you were ready for a fashion shoot. Richie is dressed like, well, Richie: brown t-shirt with a brown pattern button down shirt, jeans and a faded black jacket and beat up sneakers. You both walk in different directions when Richie suggests you both get in his car. 

You coldly respond, “If your car is anything like you, I will not be seen sitting in it.” 

“Hey, listen, I’m on sabbatical, I don’t have to look good to anyone while I’m on vacation. Is this to your liking, madam?” 

Richie points to his apple red porsche with the drop down roof and your eyes bulge,

“Oh shit...Hell yes,” Richie opens the car door for you to slide in. The leather interior cools your bottom and you nearly moan with pleasure. 

Richie slides into the driver’s seat and notices this, “Is that purring? Are you purring?” 

You close your eyes and nod your head with a smile, “Mmhm.”

Richie shifted in his seat, trying to adjust to the growing length in his jeans just watching you purr next to him, “Um...why?” 

With no thought to it, you open your eyes with a sultry gaze into his eyes, “I love fast cars..”

Richie with a deadpan expression, “Well, then. Let’s see what this bad boy can do.” Turns the ignition, steps on the gas, screeching out of the parking lot and onto the empty road. 

35.  
50.  
65.  
75 mph. 

There was something about fast cars that just turned you on. You look over to Richie driving intently down this winding road and the vibration from the engine was getting you wet. You press your thighs together and bite your lower lip. It’s all such a rush!

Richie glances over at your thighs and sees you rubbing them together, his dick stiffens, “Hey, uh, you, uh…should we...pull over?” he clears his throat, hoping the suggestion of road side sex would be something you’d be in the mood for. Just as your hooded eyes meet his with a smirk, the car speaker began ringing knocking Richie and you out of your intense moment. 

He looks at the car’s digital dash, “It’s Beverly.” He presses a button on the steering wheel and puts on his delighted voice, “HEY, BEVY! We’re on our way!” 

“Hey, Richie! Whose ‘we’?” she answers on the other line. 

You chime in, “Me! I’m riding in with Richie.” 

Beverly happily squeals, “Yaaay! I can’t wait to see you both! The gangs all here. We’ll see you soon!” 

Once the phone hangs up, uncomfortable silence filled the car. Both embarrassed at how turned on you were, nothing was said for the next 20 minutes until you reached the restaurant for brunch. 

*

Richie pulls into the parking lot of a cute little bistro in town. Richie opens the car door for you, lending you a hand to climb out. You stand up and straighten your sundress, he holds out an elbow for you to wrap your arm around, “My lady?” 

You try to stifle your smile and take his arm as you both walk arm in arm into the bistro toward the backyard seating area where Beverly and the rest of the Losers were waiting. As you walk, you can't help but feel a little nervous. You haven’t seen these people in over 20 years and the only person you ever kept in contact with was Beverly. Suddenly, you are ripped from your nerves when you hear a gleeful scream. Beverly rushes up to you, squealing and wraps her arms around you. 

“OH MY GOD, [Y/N], I’M SO HAPPY YOU’RE HERE!” she screams. 

You wrap your arms around her, “You look so beautiful! Your hair is as red as ever! I’ve missed you so much!” 

Beverly lets you go, “You look absolutely gorgeous! You haven’t changed! Doesn’t she look gorgeous, guys?” She steps back so the rest of the group can step up to greet you. 

“Hey, can I get one of those hugs?” Bill smiles big with his piercing blue eyes. 

“BILL! HEEEY!” you gleefully accept and give him a hug. 

Next in line is Mike, “Mikey...you never grew out of that kind face,” you place a kiss on his cheek. “It’s good to see you, [Y/N]”. 

You see Stan standing off to the side, a bit shy, “Come over here, Stanny!” He smiles and gives you a light hug. 

Next is Eddie so you hold up your hand for a high five, he stands there, puzzled. 

“Well?” you joke, “I know you’re not going to give me a hug because I might be carrying some kind of super bug or flesh eating virus or whatever so I'll settle for a high five.” 

Eddie chuckles and shakes his head, “Oh, no, I’ll take one of those hugs everyone’s getting.” He pulls you in for a bear hug.

Your eyes dart around with concern, “Where’s Ben?” 

A tall, handsome muscular man steps out into the light, “I’m right here.” He walks up to you as your mouth drops and eyes widen in surprise. 

“BEN?!” 

“In the flesh. Well, a lot less flesh,” he hunches down a little to hug your short frame, you inhale his cologne of leather and sandalwood. 

“You look….incredible….I...have no words…” you stammer when Richie pipes in from the background. 

“Hey, everybody, Richie’s here, too. Yaaaay,” he playfully includes himself with everyone fawning over you. 

“How can we ever forget about you, Trash Mouth?” Bill gives him a hug as do the rest of the guys. 

Eddie comments on Richie’s outfit, “Wow, Richie, you really shouldn’t have gotten so dressed up for the occasion.” 

“What can I say? Your mom ripped off my good clothes in the throes of fucking last night,” he bluntly retorted.

Eddie tightened his lips, “Not cool, man. Not cool.” 

*

After reacquainting with everyone, you felt more at ease (it could also have been the 3 mimosas you had to drink as well). It was like none of you ever left Derry. Sitting around a wrought iron circle table, sipping away at countless mimosas and bellinis, everyone began reminiscing about old times, retelling stories that were once forgotten. Drinks were spewed out onto the table from laughing so hard, old memories were coming to light and new ones were being made. You can’t remember having a better time. You also can’t remember Ben being so hot. Ben, being so hot and presently sitting to your right, every so often glancing at you with that killer smile. Making you giggle as you playfully nudge him on his arm all the while Richie sat to your left, watching you giggle like a schoolgirl, knowing full well you were crushing hard on Ben. Richie’s heart sank a little but he didn’t let it get him down, so he did what he did best in awkward situations like this: pick on you. 

“Here, [Y/N], take my handkerchief..” he hands it to you. 

You take it and stare at it, “Why are you giving this to me?” 

Richie raises both his brows, “To soak up the drool dripping down your chin from sitting next to Ben..here, let me get that for you…” he proceeds to wipe invisible drool from your chin and you slap his hand away. 

Your face red, “Shut up, Richard.” 

“Oh,but for once, I’m not talking. In fact, the only one who hasn’t shut up since we got here is you. Talking to Mr Perfect,” he rolls his eyes and looks at the others for backup jokes but everyone looks away, uncomfortable. 

“What is your problem, Richard? I’m having a good time. Who are you, my dad?” you snap back. 

“Why don’t you have another mimosa to keep your courage going?” 

Beverly intervenes with a stern voice, “Beep, beep, Richie.” 

You stand up in anger, “FUCK YOU, TRASH MOUTH!” 

Richie stands up and begins walking away with his hands up in defeat, “You’re right, I’ll go fuck myself..let Ben bring you back to the hotel...I’m outta here.” He turns to walk out but spins around to finish you off, “Oh, and by the way, we can totally see your nipples through that cheap dress!” 

You gasp, face turning beet red as you quickly fold your arms over your chest in embarrassment. 

*  
A couple hours later, Ben dropped you off at your hotel. Upon entering the lobby, Jan, the hotel staff concierge calls to you, “Excuse me, Ms [Your last name]?” You walk over to the counter and she hands you a note, “This note was left for you by the gentleman you were staying with.” 

Your eyebrows crinkle as you open the note which read:  
‘“[Y/N],  
I have left the suite, you can have it all to yourself.  
I’ve booked the room next door so you won’t have to see me until the wedding.  
Smell ya later.”’

You sigh, crumpling up the note and walk up the stairs. You knock on the door next to yours where Richie is now staying.  
You knock again.  
No answer.  
You yell beyond the door, “If you wanna be a prick, fine! I’m the one that should be furious with you acting that way, embarrassing me in front of everyone!....you’re such a fucking child, Tozier!” 

The old hotel janitor passes by you with his push broom and grumbles to you, “You wastin’ your breath, lady. The occupant in that room left the hotel an hour ago.” 

“Oh.” You sink your shoulders in disappointment getting all riled up for nothing and walk next door to your room. 

~~~  
It’s the night before the wedding and you haven’t seen or heard from Richie since that day at brunch. You did hear some noises and talking in his room through the walls that linked your rooms. You even heard him hosting a female guest to which you kept your ear glued to the wall the entire night. It sounded like they were having fun. The woman was laughing a lot then a few hours later the laughter turned into moans of pleasure. Eavesdropping and picturing Richie pleasuring another woman got you hot and bothered. You were a little jealous if you had to be honest. A part of you wanted to be in her place. You don’t know why. Not that you cared...or do you? Richie didn’t even show for the pre-wedding dinner with the rest of the Losers.

One thing’s for sure, the wedding tomorrow will be super awkward.  
~~~


	2. Backtracking

**Summary for the Chapter:**

> Beverly's wedding has arrived and the Losers gather one last time to celebrate.   
> But where's Richie?

It is Saturday afternoon, the day of the wedding. As the Maid of Honor, you have been running around all morning helping Beverly calm her nerves and run last minute errands for her as the hour arrives. After an exhaustive morning, you and Beverly kick the wedding planner and photographer out of the bridal suite so you both can take a breather. You both are on the king sized bed in big white fluffy robes, laying on your sides facing each other. 

You just stare at the beautiful soul that is your best friend, “Are you nervous?” 

“I’m a wreck but I’m more excited than nervous. I’ve waited all my life for a man like Dave and I finally found him. If it hadn’t been for Richie, I would’ve never had the chance to meet him,” she smiles warmly. 

“Richie introduced you two?” 

“Yup. I owe it all to him.”   
You prop your head up on your hand, “I have to ask. Richie says you are the only reason why he came back to Derry. I asked him if you guys ever hooked up but he evaded the question…” 

Beverly frowns a bit and sighs, “Well. While we were never involved, we did confide in each other a lot…” 

“Really?” you ask concerned. 

“Richie didn’t have such a great family life. Both his parents were alcoholics growing up and when Richie was 16, he…..” her voice trails off and she sits up. 

You sit up as well, searching her face, “He what?”

She turns to you with a single tear rolling down her freckled cheek, “He tried to kill himself.” 

You gasp, your throat clenching with sorrow, “What?!” 

She wipes away the tear and nods, “Yeah. That year was pretty rough for him. He was failing his classes, his parents were constantly arguing and putting him down. He felt like no one wanted to be around him. Why do you think Richie constantly tells jokes? Because jokes help masks the depression and sadness.” 

“I had no idea...why didn’t you tell me this was happening?” 

“Because, [Y/N], you were busy being the top of our class and getting into good colleges. I made a promise to Richie that I’d never tell another soul. Our home lives were both shitty so we related to each other. Ever since then, we’ve never lost contact.” 

You hang your head down in shame, “Beverly, I’m the shittiest friend. I should’ve picked up on this. I was so mean to him all those years ago. And after 27 years, I’m still treating him like shit!” 

Beverly sits next to you, “Hey, no..listen. You didn’t mean it. How were you to know about Richie? And I can assure you with every fiber of my being that I am not the only reason why he came to my wedding.” 

You shoot her an incredulous look.   
Beverly smiles widely and shoots up in excitement, “Now let’s get dressed and marry me!” 

*

Two hours later, you are in the short bright yellow strapless dress Beverly picked for you (not your favorite color but okay) and you are escorted down the aisle by her groom’s brother. You stand at the head of the small crowd of people and see Mike, Bill, Stan, Eddie and Ben, but no Richie. You try not to make it obvious that you’re searching the room for him but Eddie notices your eyes wander and catches your eye and mouths to you, “What?” from across the room. You give him a small embarrassed smile and shake your head that it’s nothing. 

And here comes Beverly dressed in a long sheer ivory wedding gown, looking radiant, holding a bouquet of light pink peonies. She is brimming with happiness as she makes her way up to you and stands in front of you. Your eyes start to blur with tears as the minister begins his speech. You’re becoming a blubbering mess in front of all these people but you try to hold it in. You lift your head to concentrate on the bride and her groom when your blurry eyes catch a glimpse of someone who wasn’t standing behind the groom a moment ago. Like he just appeared or maybe you hadn’t noticed the first time. 

You brush away the tears and blink a few times adjusting to see.   
It can’t be him. You squint a bit and see the person standing behind Dave is a cleaned up Richie Tozier. His long wavy hair was now short and combed to the side, he didn’t have on his glasses and he was wearing a black neatly pressed 3 piece suit with a long black thin tie and shiny black shoes. He still had his signature five o’clock shadow though. 

Your breath caught in your throat, your mouth dropped in awe of how different Richie looked. He stood there listening to the vows being exchanged with a stoic expression, not paying any mind to you. It was like you didn’t exist to him. You look away, feeling shame and guilt. Now that you were both in the same room, you can’t face him. You start to remember the things Beverly told you earlier that day and want to cry again. 

Before you know it, everyone is in an uproar of applause- the bride and groom are kissing, they are running down the aisle hand in hand with everyone behind them. You snap out of your funk and try to run ahead before any of the Losers get to you. You run into the bathroom to fix your makeup… and maybe hide away for a half hour until people got more drunk and wouldn't notice you.   
And that’s exactly what you did. 

*

After an hour of hiding in the ladies’ room and constantly being mistaken for a washroom attendant, you decided to leave and go to the free bar. 

You ordered a whiskey neat as you sat on a bar stool with your back turned against the happy world dancing to 80s music behind you. You can see the party just fine through the reflection of the mirror behind the bartender. You are too embarrassed to show your face, you don’t want Richie to see you. You take another deep gulp of whiskey when a voice behind you interrupts your wallowing. 

“It’s bad luck for a pretty lady to drink alone.” 

You look up at the reflection behind the bar and see it is Richie standing behind you, his hands tucked into his trousers. You look back down at your drink as Richie orders himself a beer and comments on your drink choice, “I’d never figure you a whiskey woman.”

Still looking at your drink, “What do you think I drink?” 

He takes a swig of beer, “I don’t know. Something girly and frilly like a Malibu bay breeze or a Cum shot.” 

You chuckle, “Cum shot is NOT a girly drink.” 

He wriggles his expressive brows, “It is the way I make ‘em.”

“Dammit, Richie!” you pout, “why are you being so cute?” 

His eyes bulge wide, “I’m not sure how to answer that…. Because I was born this way???” 

You shake your head, “No, I mean...why are you still being nice to me after years of ignoring you and being so cold to you?” 

Richie shrugs, “I don’t know. You’ve always been an uptight, stuck up little bitch but I never took it personally.” 

You couldn’t help but laugh out loud which made Richie jump in surprise, “Heeey! That’s a laugh! You’re laughing! You have a weird laugh so that means it’s a genuine laugh.” 

You playfully slapped him on his arm, “Oh, shut up!” 

He assures you, “No, no, I like when a girl laughs like a seal. It’s very attractive.” 

In the middle of your second laugh fit, Madonna’s “Crazy For You” begins playing on the speakers. Richie offers you his hand with a warm smile. 

“Oh, I don’t know...I don’t want people to look at my ugly colored dress.”

“What’s wrong with your dress?” he looks at you. 

“I look like a bottle of mustard.” 

“I wouldn’t say a bottle of mustard more like a sexy slice of cheese.” 

You gently take it and he leads you out onto the middle of the dance floor. You place your hands on his broad shoulders and he places his hands on your waist. You both start to sway to the music as you gaze up into his eyes. 

“You, uh, you clean up nice, Trash Mouth,” you sheepishly admit.

“I told you. I'm on vacation. When I’m away from the spotlight I don’t dress like my ‘TV persona’,” he smirks. 

There was a pause before Richie spoke again, “You remember this song playing at Bill’s first boy-girl party?”

You giggled, “Oh, gosh, yes!” 

He slowly exhales, “I asked you to dance but you turned me down.” 

You cringed, “I’m sorry.” 

“That’s all right. Though you did tell me you couldn’t dance because you were on your period and it wouldn’t allow you to dance or talk to me so for years I thought girls never spoke to me because they were constantly on their periods,” he smirks and shrugs. 

You throw your head back in laughter and look into his eyes, “I don’t think I’ve ever seen your eyes more blue,” you smile. 

“That’s because my eyes were hiding behind 3 inches of bullet proof glass since I was 5.”   
At this moment, Richie pulls you into him, pressing his body flush with yours. You wrap your arms around his neck, he places his hands on your hips. Your head rests on his chest as you both sway silently for a minute when Richie sees Ben off the side of the room, alone, watching everyone dance. 

Richie scrunches his lips to the side in thought, “Hey, you think you should dance with Ben?” 

You look over to Ben standing alone then look back up at Richie, his eyes soft and sympathetic. “You want me to dance with Ben?” 

“If you want to. I mean, he looks lonely...maybe you should..” he looks down at you with big soulful blue eyes. 

You grab Richie’s cheeks and pulled him down, crashing your lips into his. After a moment, you pull away and look up to see his eyes wide and bewildered. He blinks in rapid succession, “What... is happening?” 

“Apparently you being thoughtful is an extreme turn on to me…” 

“Maybe I should force you to dance with other men more often.”

You pull him down for another kiss, this time deeper, your tongues lingering longer within each other’s mouths. The taste of whiskey and beer intermingle in the most intoxicating way. You feel Richie pressing his body closer into you, you moan into his mouth. Once the moan escaped into his mouth, you could feel his erection grow harder and harder on your hip. He pulls away first and his eyes burn into you. You bite your bottom lip, he clenches his teeth, accentuating his jawline. 

You ask in a low voice, “What do you wanna do?” 

“You.” 

You stare at each other with a thick pause before you burst into laughter and his face turns red, “I’m sorry, that line sounded A LOT cooler in my head…” 

Richie grabs your hand and pulls you out and away from the dance floor and crowd. 

“Where are we going?” you call you as you are trying to run in heels. 

“My car!” he eagerly calls back. 

“No! Your car is too small! Follow me!” you pull him back into the lobby and up the stairs. 

You open the door to your hotel room and push Richie up against the door to close it. You ravage his mouth as you pull off his jacket and unbutton his vest without breaking the kiss. Once his vest is pulled off, you button his shirt and pull it off. You step back in awe of his muscular shoulders, defined chest and abs. You can’t close your mouth. 

Richie’s hairy chest is heaving as he slowly walks closer to you. His arms at his sides, his low voice vibrating by your ear, “Take off your panties.” You start to pant and do what he says.

Richie stands in front of you, his once playful eyes now dark and hungry. Without hesitation, he swiftly lifts your thigh and wraps it around his hip. You wrap your arms around his neck while his other hand snakes between your bodies and finds its way into your slick hole. You throw your head back with a moan. He slides his three digits in and out oh so slowly, his thumb massaging your swollen clit. 

He growls near your mouth, “Do you remember when we did this at summer camp?...we snuck away from the group into the closet... The way you let me touch your pussy just like this…” 

You nod and lick your lips. 

He hisses into your ear, "Yessss...just like thissss…I didn’t wash my fingers for hours just so I could go back to my bunk…..smell your pussy on my fingers and jerk off thinking about you….”  
“Fuck…” you mutter as your hips press deeper into his hand, your mouth dry from all your heavy breathing. 

You finally gain some sense of self control and grab his face, pulling him down for a kiss. You hump his hand as you take a small nip of his bottom lip, making him suck in his breath, “Ah.” 

“Oh, I’m sorry,” you quickly apologize. 

“No, I’m sorry,” Richie lets you go and calmly walks over to the king sized bed, sitting on the edge with a straight face, looking at you, “I’m not going to let you cum until you sit on my face.” 

You raise your brows in surprise, you’re dripping down your thigh as you struggle to walk in a straight line over to him on the bed. Richie smirks as he lays on his back and offers his hands out to you to hold as you climb over his torso and delicately place your knees on either side of his head. You look down at him, a bit worried and scared that you’d suffocate him. You’ve never straddled a man’s face before! 

Richie looks up at you with hooded eyes and a killer smirk, “Don’t worry, [Y/N], I know how to swim…I just want a little taste….” 

You take a deep breath and gently squat down when Richie wraps his arms around your hips, pulls you down onto his face and LOCKS his arms around you so you can’t move. His mouth acts as a vacuum and sucks your clit into his mouth. Your once neatly brushed hair flips back as you scream out in pleasure. His tongue darts in and out of your wet hole while he moans deeply inside you, sending waves of heat throughout your body. You’re trying to grasp at anything around you to keep balance, you feel like you’re about to lose it. Richie notices this and lets go of your hips and lends you his hands for you to hold onto as you began bouncing lightly onto his mouth. You can hear him muffling ‘yes, yes’ beneath you when you decided to lift up off of his face, turn around and bend over to undo his belt and zipper. 

Richie sits up on his elbows to continue eating you and your ass when you shove his trousers and boxer briefs down to his knees. His long thickness nearly poked you in the eye once exposed. You salivate at the girth and lick your lips, you comment, breathlessly, “My God, you’ve got a huge dick…” 

He makes a joke, “I always told the guys they’re lucky we’re not measuring dicks….”   
You roll your eyes, “Beep, beep, Richie,” before plunging his dick into your hot mouth, making him buck his hips up into your mouth. 

“Fffffffuuuuuuck, yeah,” he lets his head drop back letting you take full control of pleasuring him then remembered your pussy is right by his mouth and proceeds to tongue his way through your folds. 

Together, fucking each other with your mouths, feeling each other’s hot breath between your thighs was the most amazing sensation you have felt in a long time. 

Richie was bucking his hips harder and harder into your face, you could feel his balls start to tighten which meant he was ready to blow a load. You couldn’t wait, you wanted to feel him cum now. But, he didn’t want to. He pulled his mouth away from your cunt, “I don’t want to finish this way….” and he shoves you off of him. 

Confused, you sit up looking at him as he takes his pants off and swiftly crawls over your body and lays on top of you while he kisses your chest, neck and face, then looks into your eyes, “I want to look at you when we come….”

You smile and nod as you both kiss deeply while he strokes himself before slowly entering you. You bite down on your lip with a slight moan and he quickly becomes worried, “Am I hurting you? Should I stop?” 

“No, no….I’m okay. Please, don’t stop….” you smile. 

Richie opens his mouth and closes his eyes, whispering, “God...you’re so ….fucking tight... it feels...amazing…” 

“Mmmmm….it’s been a while….” you giggle as he thrusts slowly, opening his eyes again to look down at you and smile sweetly. 

“You’re so beautiful.”

“So are you,” you reply, feeling your toes beginning to curl, “Oh God…..I…..I think I’m gonna cum…” 

“Yeah?” he speeds up the pace, looking down at your breasts popping out of your yellow dress with each thrust, jiggling with every movement he made, “Fuuuuck….” he lowers his head down to take your left nipple into his mouth and sucks on it while pushing into you faster and faster. 

“Fuck, Richie! Yes! YES!” you start to scream as his tongue slithers from one nipple over to the next and up your neck to your ear. 

He muffles into the crick of your neck, “Ah, shit...ummf..ummmf...FFFFFFFFFFFFFFUUUUUUUUUUCK!” His hips buckle into you one more time, filling you up before collapsing on top of you, winded and sweaty. 

After a couple of minutes laying still inside you, he rolls off of you and onto his back. You both stare up at the ceiling with sweaty smiles on your faces, both out of breath. 

Richie broke the silence, “Dude, we totally 69’d.” 

“That was fucking hot,” you snuggle up against his chest and giggle. 

“Yeah, it was!” he holds up his hand and you high five. 

You sigh out loud with a hint of sadness, “Everyone goes home tomorrow…everything’s gonna go back to boring normal after tonight.”

Richie furrows his brows, “You make it sound so final. We’re definitely seeing each other again.”

You look up at him, “Really?” 

“Of course. We’ll make it work. You think I’m gonna let you go now that I finally have you? No, ma’am. My dick found a new home!” 

You chuckle then remember something from the other night, “Speaking of your dick finding a new home, when you moved to the room next door, I heard you with a woman one night. And she was...screaming with passion….who was that?” 

Richie exhales, “Yeeeeah, she was a friend I called over. I, uh, knew you were listening so I...I asked her to pretend we were having sex to make you jealous…” 

You sit up, “Seriously?” 

He nods, “Yeah. Did it work?” 

You jump on top of him, straddling his hips, “Yes.” You lower your head and kiss him on the lips. 

His soft eyes look up at you, “Hey. Do you wanna come back with me to LA? Visit for a couple days? You can stay at my place, hang around, we can 69 anywhere in my house. It’ll be rad.” 

Your smile gets bigger as does your heart, “I’d love to go back to your place.” 

He excitedly smacks your ass, “Hurray! Go pack your shit, we can leave tonight!” 

You plant a big sloppy kiss on his forehead and jump off the bed, “Yay! I’m halfway packed. I just left some clothes on the bathroom floor.” You scuddle to the bathroom as Richie places his hands behind his head and sighs with content. ‘Everything’s coming up for me,’ he smiles to himself looking at the ceiling. 

You shout from the bathroom, “What’s all this hard, crusty stains on my bra and clothes?” 

Richie’s eyes bulge from his sockets as he remembers what he did, “Uuuh, about that…”

**Notes for the Chapter:**

> Thanks again for reading! Sorry for the sloppy editing, I just wanted to get this out of my brain before the busy holidays!


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